Professional Documents
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May 2014
FOREWORD
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H. A. Maini, RPh
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Laboratory gown
Laboratory shoes
Head cap
Safety goggles
Face mask
Gloves
Chemical Hazards
Every chemical is a poison, depending on the dose taken. We handle
hazardous chemicals in our everyday lives, from the gasoline we use to run
cars to using chlorine bleach to clean the laundry. The keys to safe use of
these and any chemical are: understanding the hazards of each chemical;
knowing and using safety measures to minimize these hazards. However, it
is easy to forget all these and treat hazardous materials casually.
Precautionary measures have to be taken seriously. Simple precautions can
be a lifesaver; use them as you use a harness when driving a car.
Liquid Chemical Hazards
Liquid chemicals present the greatest potential risk for injury:
1. they have to be handled (transported, poured, and mixed) to be
used;
2. theres a wide variety, each with a different set of hazards and
precautionary
measure required for use.
Chemicals in the laboratory can cause severe burns, tissue, and organ
damage, and can ignite and explode. The greatest health risks posed by
liquid chemicals are physical (fire, explosion), direct contact with skin and
eyes (tissue damage), and inhalation (pulmonary damage or long term
chronic effects).
For detailed hazard information, consult the pertinent MSDS.
Make every effort to understand the chemical processes you use and
respect the chemicals you work with. Knowing the general rules on how to
safely transport, pour, use, and dispose of these chemicals is every
laboratory user's responsibility.
Gas Hazards
Compressed gases pose both chemical and physical hazards. Some of
the gases used are inert; others are toxic, corrosive, flammable, or explosive.
The primary health risks posed by gases are the physical hazards (fire,
explosion) and inhalation (toxins and corrosives). Because of these potential
hazards, as a laboratory user, one must be always aware of the types gases
and the hazards posed in the equipment being used.
Electrical Hazards
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exposure to corrosives, one should get help. The victim should be taken to
the emergency center for evaluation and treatment.
Oxidizing agent
An oxidizing agent is a chemical compound that has a pair of electrons
to donate to an electron-accepting, reducing agent. Often, they contain
reactive oxygen. When mixed with compounds that can act as reducing
agents, the result is often a violent reaction, possibly an explosion.
Oxidizing agents should not be stored or mixed with solvents, which
generally make
excellent reducing agents. Oxidizing agents are stored in the chemicals passthrough. One oxidizing agent is hydrogen peroxide (H2O2). Nitric acid
(HNO3) is an oxidizing agent as well as a corrosive.
In the laboratory, the main principle behind segregation of chemicals is
to keep oxidizing agents away from flammable chemicals (namely, solvents)
and any combustible materials (some chemicals, materials like laboratory
wipes).
Water reactive
Water reactive describes compounds which very quickly generate heat
and/or gas upon mixing with water. These are often concentrated acids or
bases. The primary hazard presented by water-reactive compounds is
incomplete mixing, which can lead to superheating and explosion. Thus,
water-reactive mixtures should never be poured directly into a sink drain.
Aspirating water reactive mixtures at the wet benches is standard
practice; the high dilution factor and rapid mixing dissipates heat and
prevents superheating.
Flammables
Flammables include most solvents, such as acetone, isopropanol, and
methanol. The flash point of a flammable is the concentration in air above
which the vapors from a flammable can ignite and explode. The source of
ignition may be heat (such as a hot plate) or a spark (such as from an
electrical tool). Because the vapors can travel over considerable distances,
the source of ignition can be far away from the flammables container itself.
To minimize hazards, always work well within the exhausted area of the
appropriate bench (behind the red line). The air pulled into the exhaust area
will keep the concentration of vapors below the flash point. Where possible,
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GROUP NO.
EXPERIMENT (DATE)
NAMES OF GROUP MEMBERS
(DATE)
START OF
END OF EXPERIMENT
I.
II.
III.
Group
20%
Products submitted
Examinations
Periodical exams 20%
Quizzes
20%
Reports submitted
Research on a synthesis
Compilation of reports
5%
40%
10%
10%
5%
Total
100%
TABLE OF CONTENTS
TITLE PAGE
FOREWORD
PROPER CONDUCT OF STUDENTS IN THE LABORATORY. . . . . . . . . . . .
........ 3
LABORATORY HAZARDS
OVERVIEW . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
Page 14 of 52
WHAT TO DO IN CASE OF AN
EMERGENCY . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
10
FORMAT OF LABORATORY
REPORT. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
12
LABORATORY GRADING
SYSTEM . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
Experiment 1. EVALUATION AND TESTING OF ORGANIC COMPOUNDS .
......
15
Experiment
2:
SYNTHESIS
ACID . . . . . . . . . . . . . . . . . . . . . . . . . . . . 21
OF
BENZOIC
Experiment 1.
COMPOUNDS
EVALUATION
AND
TESTING
OF
ORGANIC
I. Introduction
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2. Phenol
3. Ethyl acetate
4. Acetone
5. Formaldehyde
6. Toluene
7. Diethylether
8. Methanol
9. Salicylic acid
10. Benzoic acid
Equipment: Melting point apparatus
IV. Special instructions
Students are expected to take precautionary measures in handling the
organic compounds to be tested and reagents to be used in this experiment.
Students are NOT ALLOWED TO TASTE sample materials unless
directed.
Students are requested to observe EXTREME CAUTION when handling
chemicals.
V. Procedure
A. Evaluation of the physical state of the sample.
1. Observe the physical state of the sample
temperature.
2. Note the color of the sample.
3. Describe the odor of the sample.
at
room
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yellow
to red precipitate
5. Formaldehyde
Perform Phenylhydrazone Test using formaldehyde as the test sample.
6. Toluene
Bromine Test
a. One ml of toluene is added to a clean and dry test tube.
b. A few iron filings is added to another test tube, followed by
one ml of toluene
to rinse down any iron filings stuck on the test tube
walls.
c. To each test tube was added 3 drops of bromine.
d. The test tubes were placed in a beaker of warm water for 15
minutes. The
color of each test tube was observed, and whether or not
HBr was evolved; and the
results recorded.
Bayers Test (use of aqueous KMnO4)
a. Five ml of KMnO4 solution is placed in one test tube.
b. Five drops of toluene is added to the test tube.
c. The test tube was shaken well for 1-2 minutes and the result
noted.
7. Methanol
CAUTION! Methanol is poisonous.
Use identity tests for ethanol.
8. Isopropyl alcohol
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Experiment 2.
I. Introduction
Benzoic acid is a colorless, crystalline solid also known as
benzenecarboxylic acid. It is the simplest aromatic carboxylic acid, with a
carboxyl group (-COOH) bonded directly to the benzene ring. It is found
naturally in the benzoin resin of a number of plants. Benzoin comes from the
bark of a number of balsams of the Styrax genus, most notably Styrax
benzoin and Styrax benzoides. S. benzoin is native to Southeast Asia, and
was traded between Indonesia and China as early as the 8th century c.e.
Benzoin was used for fragrances, spices, medicines, and incense. Today most
benzoin comes from Sumatra (Indonesia) and Laos. Healthy trees do not
produce benzoin, but an incision or wound injuring the cambium results in its
secretion.
CHEMICAL NAME = benzoic acid
CAS NUMBER = 65850
MOLECULAR FORMULA = C7H6O2
MOLAR MASS = 122.1 g/mol
COMPOSITION = C(68.9%) H(4.9%) O(26.2%)
MELTING POINT = 122C
BOILING POINT = 249C
DENSITY = 1.3 g/cm3
II. Objectives
This experiment aims to:
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graduated cylinder
beaker
30-40% HCl
Toluene
KMnO4
pH paper
plastic basin
water pump
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Fig. 1 Reflux set-up. (The heat source is a sand bath, placed on top of a
hotplate.)
Once the reaction is completed, the solution above the formed
manganese dioxide precipitate must be colorless. If not, discoloration of the
solution may be achieved by adding 1 ml alcohol or 0.5g oxalic acid while
heating. This will quickly reduce the remaining potassium permanganate in
the mixture.
The resulting solution is then filtered by suction or through a coffee
filter and the obtained precipitate washed with hot water. The resulting
filtrate is placed in a suitable beaker and the filtrate evaporated to about 50100 ml with the use of a water bath and again filtered to remove the newly
formed manganese dioxide. Wash the obtained solid with 5 ml of hot water
and cool the combined filtrate to room temperature. The combined filtrate
was acidified with concentrated HCl until it produces an acidic reaction to pH
paper. The acidity of the reaction mixture will allow the formation of benzoic
acid crystals from solution.
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REPORT SHEET
Experiment No. and Title
Name of the student/s:
performed:
Section and Group No.:
submitted:
Date
Date
Theoretical Data
Actual Data
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Physical appearance
Melting point/Boiling
point (as the case
maybe)
Solubility
Yield
Percent yield
Tests for Identity
VI.
Qestions to be answered:
1.
What is the mechanism of reaction involved in the preparation of
benzoic acid?
2.
Give at least five (5) physico-chemical parameters used to ascertain
the identity of
benzoic acid. Include chemical reactions (if there is any)
3.
Identify the uses of benzoic acid.
4.
Provide plant sources where benzoic acid can be found.
5.
Give at least five official preparations where benzoic acid is an integral
part of. For what are the named preparations used for. State where these
named preparations are
official.
VII.
Reference used
Myers, R. L. (2007) The 100 Most Important Chemical Compounds: A
Reference Guide.
Greenwood Press: London.
Experiment. 3
I.
INTRODUCTION
Sulfa drugs were discovered in the early 1900s and were found
to be active as antibacterial agents. Sulfanilamide inhibits the
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II.
III.
OBJECTIVE
:
To synthesize sulfanilamide from aniline.
INSTRUCTIONS:
A. Read on the physical properties (physical appearance and
melting point) of the intermediates and the product.
B. Look for chemical tests that would identify the intermediates and
the product.
C. Read on techniques for heating, vacuum filtration, decolorization,
crystallization and recrystallization, purification and melting point
determination.
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REAGENTS
Aniline
Sodium acetate
V.
Conc. HCl
Chlorosulfonic acid
Conc. HNO3
Sodium
bicarbonate
Distilled water
Acetic anhydride
Conc. Ammonia
Ice water
CHARACTERISTICS
Irritant, corrosive
Hazardous gas, caustic and corrosive
Irritant to the eyes and skin, harmful if
ingested and inhaled and a possible
carcinogen
Irritant to the eyes and skin
Corrosive and reacts violently with water
Irritant especially to respiratory system
VI. PROCEDURE:
A. Acetanilide
1. Dissolve 1 gram of aniline in 30 ml of distilled water and I ml
of conc. HCl in a 125 ml Erlenmayer flask. If the solution is
colored, vacuum filter through decolorizing charcoal.
2. Measure out 1.2 ml of acetic anhydride and prepare a solution
of 1 gram of sodium acetate in 6 ml of distilled water.
3. Add the acetic anhydride to the solution of aniline with
stirring, and at once add the sodium acetate solution.
4. Stir the mixture, cool it in ice, and collect and weigh the
product acetanilide.
NOTE: The material needs to be completely dry before the
next step.
Characterize the acetanilide.
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B. p-Acetamidobenzenesulfonyl chloride
1. Place 0.5 gram dry acetanilide in a dry 25 ml Erlenmayer
flask.
2. Add 1.25 ml of chlorosulfonic acid(Org13) (WARNING!
Corrosive and reacts violently with water) a few drops at
atime using a Pasteur pipette (CAUTION! No metal needles!).
3. After about 10 minutes, the reaction should subside and
almost all of the acetanilide should have dissolved.
4. Heat the mixture in a hot water bath for about 10 minutes to
complete the reaction.
5. Pipet the mixture slowly with stirring into 7 ml of ice water in
another 25 ml Erlenmayer flask (WARNING! USE EXTREME
CAUTION WHEN DOING THIS!)
6. Rinse the reaction flask with cold water and stir the product
until an even suspension of white solid is obtained.
7. Vacuum filter the p-acetamidobenzenesulfonyl chloride and
wash it with water.
C. p-Acetamidobenzenesulfonamide
1. Transfer the solid (you can use the solid even if it is wet) to
the rinsed 25 ml Erlenmayer and add 1.5 ml of concentrated
ammonia and 1.5 ml of distilled water.
2. Heat the mixture to just below the boiling point on a hot plate
with occasional swirling for 5 minutes.
3. Cool the mixture in an ice bath and collect the pacetamidobenzenesulfonamide by suction filtration and allow
it to drain thoroughly.
D. Sulfanilamide
1. Transfer the moist solid to a 25 ml Erlenmayer.
2. Add 0.5 ml of conc. HCl and 1 ml of water.
3. Boil the mixture gently until the solid dissolves and then
continue heating at the boiling point for about 10 minutes
longer (do not evaporate to dryness).
4. Cool the solution to room temperature. No solid should
deposit. If the solid material is seen, continue heating
for a little while longer.
5. To the cool solution, add a saturated aqueous solution of 0.5
grams of sodium bicarbonate until the solution is neutral to
pH paper.
6. Cool the mixture in ice and vacuum filter the sulfanilamide.
Characterize the product.
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REPORT SHEET
Experiment No. and Title
Name of the student/s:
performed:
Section and Group No.:
submitted:
Date
Date
ACTUAL DATA
Physical appearance
Melting point
Solubility
Yield
Percent yield
VII.
Computations:
1. Determine the theoretical yield of the intermediate and the
product in your preparation.
2. Calculate the percentage yield of your product using the formula:
Percentage yield =
Actual yield
Theoretical yield
VIII.
100
Questions to be answered:
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SYNTHESIS OF ASPIRIN
INTRODUCTION
Historically, the salicylates were among the first drugs to achieve
recognition as analgesics. In the 17 th century, the extract of willow,
Salix spirea, was found to produce fever-reducing properties and
was used by Jesuit missionaries (Bailey, Jr. and Bailey 1998). In
1827, Leroux isolated salicin (I), the active principle in the willow
bark and Piria, in 1838, prepared salicylic acid (II) from salicin. By
1860, Kolbe and Lautermann prepared it synthetically from phenol
(Willette 1991). Although salicylic acid is an effective antipyretic, it
causes severe stomach irritation in some people and for this reason
the research for a pain reliever continued in the late 1800s (Bailey,
Jr. and Bailey 1998). Aspirin, chemically known as acetylsalicylic
acid, the salicylate ester of acetic acid, was first prepared in 1853
by Gerhardt, but remained obscure until Felix Hoffmann, who
worked for the Bayer Company, discovered its pharmacologic
activities in 1899 when he used the acetyl derivative on his father
suffering from arthritis. The name aspirin comes from spirin, an old
name of salicylic acid or spiric acid, derived from its natural source
of spirea plants (Willette 1991). Unfortunately, even aspirin causes
stomach distress in some individuals and minor, usually clinically
unimportant, gastric or intestinal bleeding (Bailey, Jr. and Bailey
1998). Nevertheless, aspirin remains, until now, the most popular
and the most versatile drug ever to have been synthesized.
Salicylates, in general, exert their antipyretic action in febrile
patients by increasing heat elimination of the body through
mobilization of water and consequent dilution of the blood. This
brings about perspiration, causing cutaneous dilatation. This does
not occur with normal temperatures. The antipyretic and the
analgesic actions are believed to occur in the hypothalamic area of
the brain. Thye antitheumatic and antithrombotic actions of aspirin
is said to arise from its selective action on the synthesis of the
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OBJECTIVES:
A. To demonstrate the process of esterification reaction;
B. To understand electronic and steric effects in esterificaton
reactions;
C. To utilize the differing rates of reactions and differences in
solubilities to optimize the yield of the desired product; and
D. To utilize chemical tests in determining the presence of functional
groups.
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III.
INSTRUCTIONS:
A. Read on the physical properties (physical appearance and
melting point).
B. Look for the theoretical results of each intermediate/product in
the chemical tests given and read on the principle involved in
each test.
C. Read on techniques for heating, vacuum filtration, decolorization,
crystallization and recrystallization, purification and melting point
determination.
D. Compute for the amounts (in grams or milliliters) of other
reactants and reagents based on the amount of starting material
that is assigned.
E. Prepare a schematic diagram for the procedure.
F. Draw the set-up necessary in the procedure. Label completely.
G. At the end of the laboratory period, pass a datasheet complete
with the computations of amounts of reactants, validated
amounts, and actual results of physical and chemical tests.
IV.
REAGENTS:
V.
PROCEDURE:
Salicylic acid
Benzene
Acetic anhydride Petroleum ether (optional)
Conc. Sulfuric acid
1% Ferric chloride
Saturated NaHCO3
Cupric acetate
Conc. HCl
95% Ethanol
REPORT SHEET
Experiment No. and Title
Name of the student/s:
performed:
Section and Group No.:
submitted:
Date
Date
ACTUAL DATA
Physical appearance
Melting point
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Solubility
Yield
Percent yield
VII.
QUESTIONS TO ANSWER:
1. What is the purpose of the concentrated acid in the acetylation
reaction?
2. Which would you expect to be a stronger acid: benzoic acid,
salicylic acid, or aspirin? Explain.
3. What is the purpose of concentrated acid in the purification of
aspirin?
4. How do the techniques of scratching and seeding induce
crystallization?
5. How is the ferric chloride test used to detect the presence of
salicylic acid? What general type of compound gives a positive
result for this test?
6. Can you use water as solvent for recrystallization? Explain.
VIII. REFERENCES:
Bailey, P.S., Jr. and Bailey, C.A., 1998. Organic Chemistry: A Brief
Survey of Concepts and Application. 5th Edition. Singapore: PrenticeHall Internaional, 393-394.
Pavia, D.L., Lampman, G.M., and Kriz, G.S., Jr., 1976. Introduction to
Organic Laboratory Techniques: A Contemporary Approach>
Philadelphia: W.B. Saunders, 25-30, 423.
Page 36 of 52
Experiment 5:
I.
INTRODUCTION
Methyl salicylate, also known as salicylic acid methyl ester, oil of
wintergreen, betula oil, or methyl-2-hydroxybenzoate, is a natural
product which can be obtained from several plant species. Some of
the plants producing it are called wintergreens, hence its common
name. Plants containing methyl salicylate produce this organic ester
most likely as an anti-herbivore defense. If the plant is infested with
herbivorous insects, the release of methyl salicylate may function as
an attractant of beneficial insects that could act as natural
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OBJECTIVES:
1. To synthesize methyl salicylate by the process of esterification.
2. To know the requisites for the esterification reaction to occur.
III.
REAGENTS:
IV.
Salicylic acid
Methanol
Conc. Sulfuric acid
REAGENT INFORMATION:
COMPOUND
Salicylic acid
Methanol
Sulfuric acid
CHARACTERIISTIC
Irritant to the eyes and skin
Toxic, CNS depressant
Highly corrosive chemical. May
cause burns.
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V.
PROCEDURE:
Place 1.0 gram of salicylic acid and 6.0 ml of methyl alcohol in a
25 ml Erlenmmayer flask. Add 4.0 drops of concentrated sulfuric
acid (REMINDER! Note the odor of the resulting solution) and then
place the test tube in a water bath previously heated to 7o degrees
and heat the solution for 15 minutes.
NOTE: The boiling point of methanol is 64.6 degrees, care should
be taken to avoiod overheating and minimize bumping.
Allow the resulting product to cool to room temperature and note
the odor before placing it in a suitable container and properly label
the product.
VI.
REPORT SHEET
Experiment No. and Title
Name of the student/s:
performed:
Date
Page 39 of 52
Date
ACTUAL DATA
Physical appearance
Melting point
Solubility
Yield
Percent yield
VII.
QUESTIONS TO ANSWER:
1. Give the general reaction for the synthesis of methyl salicylate.
2. Propose a reaction mechanism for this synthesis.
3. Provide the physico-chemical characteristics of the product.
4. How can the product be tested by chemical means? Include
pertinent chemical reactions.
5. What physico-chemical methods can be resorted to, to identify
methyl salicylate? Provide the characteristic IR and NMR spectra
for this compound.
I.
INTRODUCTION
Azo dyes, the most commonly employed of all kinds of dye can
be prepared by azo coupling. This is due to the fact that aryl
diazonium ions (ArN N+) are weak electrophiles and give strongly
colored compounds (ArN=Nar) by electrophilic substitution, but
only on aromatic rings which are strongly activated by hydroxyl or
amino groups. Most dyeing operations utilize hot aqueous solutions
of the dyes, many of which bear sulfonic acid groups to improve
their water solubility. Two dyes will be prepared in this experiment.
Sulfanilic acid will be diazotized by reaction with nitrous acid, and
the resulting diazonium-sulfonate inner salt will then be coupled
with 2-naphthol and N,N-dimethylaniline to give the dyes commonly
known as Orange II and Methyl orange, respectively.
II.
REAGENTS:
For diazotization and synthesis of Orange II Dihydrate:
Sulfanilic acid monohydrate
Sodium nitrite
Concentrated HCl
10% aq. NaOH
Distilled water
REAGENT INFORMATION:
COMPOUND
Sodium nitrite
Conc. HCl
N,N-dimethylaniline
Glacial acetic acid
IV.
CHARACTERIISTIC
Decomposed even by weak acids
with the evolution of brown
fumes
Irritant; corrosive
Poisonous!
Eye irritant
PROCEDURES:
Procedure for diazotization of sulfanilic acid
Page 41 of 52
Page 42 of 52
Page 43 of 52
REPORT SHEET
Experiment No. and Title
Name of the student/s:
performed:
Section and Group No.:
submitted:
Date
Date
ACTUAL DATA
Physical appearance
Melting point
Solubility
Yield
Percent yield
VI.
QUESTIONS TO BE ANSWERED:
1. Draw the structure of methyl orange at acidic and basic pH, and
underneath each structure, indicate the color observed for each
compound.
2. What are the methods of fabric dying?
3. What are mordant dyes? Explain how mordant dyes adhere to
fabrics.
Page 44 of 52
Experiment 8:
I.
INTRODUCTION
Banana oil is the common name of the chemical compound
properly known as amyl acetate also known as isopentyl acetate. It
is a colorless liquid ester derived from amyl alcohol. It resembles
the smell of bananas but is not naturally found in banana fruit.
II.
REAGENTS:
III.
PROCEDURE:
1. Place 15 ml of isopentyl alcohol in a 100 ml round-bottom flask
and add 20 ml of glacial acetic acid.
2. Swirl the flask and carefully add 4.0 ml of concentrated sulfuric
acid (Caution! Highly corrosive).
3. Attach a reflux condenser and, using a heating mantle, reflux the
mixture for 1 hour (do not forget to add boiling chips). Cool to
room temperature.
4. Place the reaction mixture in a separatory funnel and add 55 ml
of cold water (Remember to rinse the reaction flask with 10 ml of
cold water and add it to the separatory funnel). Separate the
lower aqueous layer.
5. Extract the organic layer (upper layer) with 25 ml of 5% sodium
bicarbonate solution twice (test to be certain that the aqueous
layer is basic to litmus otherwise wash again). CAUTION!
Formation of carbon dioxide which will exert pressure inside the
separatory funnel.
6. Extract the organic layer with 25 ml of water. Finally, add 5.0 ml
of saturated aqueous NaCl to aid in layer separation (it removes
traces of water from the organic layer). Do not shake this
solution but simply swirl. Draw off the lower aqueous layer. Pour
Isopentyl alcohol
Glacial acetic acid
Conc. Sulfuric acid
Distilled water
5% Sodium bicarbonateSaturated aq. NaCl solution
Anhydrous magnesium sulfate
Page 45 of 52
the top organic layer into an Erlenmayer flask and dry with 2
grams of anhydrous magnesium sulfate.
7. Decant the ester into the distilling flask (make sure that the
drying agent is excluded and all glassware completely dry). Set
up the distillation apparatus. Be certain that the adapter is open
to the atmosphere and that your thermometer is placed correctly
in the distilling head(do not forget the boiling chips). Collect all
distilled material but collect the fraction between 134 and 143
degrees in a separate tared flask. Keep the receiver flask cold to
reduce the vapor escaping into the lab environment. Never distill
to dryness. Record the barometric pressure in the laboratory.
8. Weigh the product and calculate the percentage yield.
IV.
Date
Date
ACTUAL DATA
Physical appearance
Melting point
Solubility
Yield
Percent yield
Page 46 of 52
V.
QUESTIONS TO BE ANSWERED:
1. Provide the chemical reaction involved in the synthesis of amyl
acetate.
2. Provide a possible reaction mechanism for the above synthesis to
occur.
3. Give reasons for the following steps:
a. swirling of the flask containing the reactants prior to addition
of sulfuric acid.
b. washing with cold water
c. extraction of the organic layer with 5% sodium bicarbonate
solution twice
d. addition of 5 ml of saturated aqueous NaCl
e. keeping the receiver flask cold
4. What are the uses of banana oil?
5. Is banana plant a tree? Justify your answer.
VI.
REFERENCES:
http://bllogcritics.org/scitech/article/what-is-banana-oil/
http://www.umsl.edu/orglab/experiments/Bananaoil.html
http://www.hort.purdue.edu/newcrop/morton/banana.html
Page 47 of 52
Experiment 9:
I.
INTRODUCTION
Castor oil is a vegetable oil obtained from the castor bean. It is a
colorless to very pale, yellow liquid with mild or no odor or taste.
Castor oil is composed of a mixture of triglycerides, about 75% of
which is tricinolein. The remainder consist of diricinoleoglycerides
with the third acyl group, representing either oleic,
linoleic,
dihydroxystearic, or saturated (stearic or palmitic) acid.
Azelaic acid is a saturated dicarboxylic acid found naturally in
wheat, rye and barley. It is a natural substance that is produced by
Melassezia furfur, a yeast that lives on normal skin. It is industrially
produced by the ozonolysis of oleic acid. It is effective against a
number of skin conditions, such as mild to moderate acne, when
applied topically in a cream population of 20%. Azelaic acid may be
useful as a hair growth stimulant, although at present there is no
clinical study to confirm the efficacy. Its antibacterial property
reduces the growth of bacteria in the follicle (Propionibacterium
acnes and Staphylococcus epidermidis). It has a keratolytic and
comedolytic property which normalizes the disordered growth of the
skin cells, lining the follicle. Azelaic acid does not result in bacterial
resistance to antibiotics, reduction in sebum production,
photosensitivity (easy sunburn), staining of skin or clothing, or
bleaching of normal skin or clothing.
II.
Page 48 of 52
III.
IV.
REAGENT INFORMATION:
COMPOUND
95% ethanol
Conc. Sulfuric acid
KOH pellets
V.
CHARACTERIISTIC
Toxic, CNS depressant
Highly corrosive chemical. May
cause burns.
Caustic irritant
PROCEDURE:
Fifteen grams castor oil is added to a solution of 15 grams
potassium hydroxide in 45 ml 95% ethanol. The mixture is placed in
a 500 ml Erlenmayer flask equipped with a reflux condenser and is
boiled for 30 minutes. Timing starts at the appearance of the first
drop of condensate. The solution is then poured into 100 ml water
and acidified by the addition of 30 ml of 40% sulfuric acid in water.
The procedure is repeated until all the ricinoleic acid have been
liberated. The acid that separates is washed until the aqueous layer
becomes clear. The yield of crude ricinoleic acid thus obtained
approximately 16 grams.
Twelve grams of ricinoleic acid is dissolved in 80 ml water
containing 4 grams potassium hydroxide. In a one liter roundbottomed flask equipped with a powerful mechanical stirrer are
placed 34 grams of potassium permanganate and 400 ml water at
35 degrees. The mixture is stirred to facilitate solution of the
permanganate, and, if necessary, heat is applied to maintain the
temperature at 35 degrees. When the permanganate has
completely dissolved, the alkaline solution of ricinoleic acid is added
in single portion with vigorous stirring. The temperature rises to
about 75 degrees. Stirring is continued for half an hour, or until a
test portion added to water shows no permanganate color. To the
mixture is now added a solution of 20 g concentrated sulfuric acid in
63 ml water. The acid must be added slowly and carefully to prevent
too rapid evolution of carbon dioxide with consequent foaming. The
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REPORT SHEET
Experiment No. and Title
Name of the student/s:
performed:
Section and Group No.:
submitted:
Date
Date
ACTUAL DATA
Physical appearance
Melting point
Solubility
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Yield
Percent yield
VII.
QUESTIONS TO ANSWER
1. Provide the chemical reactions involved in the preparation of
azelaic acid from castor oil.
2. Propose the mechanism of reaction involved based on the
provided chemical reaction.
3. Characterize castor oil. Provide the botanical origin of the plant
source.
4. Provide the names of 5 plant acids found in castor oil and give
their chemical structures, as well as their IUPAC names.
IX.
REFERENCES:
Bailey, P.S., Jr. and Bailey, C.A., 1998. Organic Chemistry: A Brief
Survey of Concepts and Application. 5th Edition. Singapore: PrenticeHall Internaional, 393-394.
Pavia, D.L., Lampman, G.M., and Kriz, G.S., Jr., 1976. Introduction to
Organic Laboratory Techniques: A Contemporary Approach>
Philadelphia: W.B. Saunders, 25-30, 423.
Wilcox, C.F., Jr. and Wilcox, M.F., 1995. Experimental Organic
Chemistry: A Small Scale Approach. 2nd Edition. New Jersey:
Prentice-Hall, 486-487.
Willette, R.E., 1991. Analgesic Agents. In: J.N. Delgado and W.A.
Remers, ed. Wilson and Gisvold,s Textbook of Organic Medicinal and
Pharmaceutical Chemistry. 9th Edition. Philadelphia: J.B. Lippincott,
657.
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